Possible Clues:

• Brothers who sang "You, You, You"
• Ed who sang 'My Cup Runneth Over'
• City on the South Skunk River
• Harry of the novel 'The Man Who Cried I Am'
• Colonial almanac compiler Nathaniel
• Les, who kept wicket for Kent
• With 61-Down, a Big 12 campus city
• City southeast of Fort Dodge
• City half an hour north of Des Moines
• University town west of Cedar Rapids